Silatrane derivative, method for manufacturing same, adhesion promoter, and curable silicone composition

Abstract

A silatrane derivative having the formula: ##STR1## wherein each R 1 is independently a hydrogen atom or an alkyl group; each R 2 is independently selected from the group consisting of a hydrogen atom, an alkyl group, and an alkenyloxyalkyl group having the general formula: --R.sup.4 --O--R.sup.5 wherein R 4 is an alkylene group and R 5 is an alkenyl group, with the proviso that at least one R 2 is an alkenyloxyalkyl group; and each R 3 is independently selected from the group consisting of a monovalent hydrocarbon group, a C 1 to C 10 alkoxy group, a glycidoxyalkyl group, an oxiranylalkyl group, an acyloxyalkyl group, a haloalkyl group, and an aminoalkyl group.

That which is claimed is: 
     
       1. A silatrane derivative having the formula: ##STR11## wherein each R 1  is independently a hydrogen atom or an alkyl group; each R 2  is independently selected from the group consisting of a hydrogen atom, an alkyl group, and an alkenyloxyalkyl group having the general formula:   --R.sup.4 --O--R.sup.5     wherein R 4  is an alkylene group and R 5  is an alkenyl group, with the proviso that at least one R 2  is an alkenyloxyalkyl group; and each R 3  is independently selected from the group consisting of a monovalent hydrocarbon group, a C 1  to C 10  alkoxy group, a glycidoxyalkyl group, an oxiranylalkyl group, an acyloxyalkyl group, a haloalkyl group, and an aminoalkyl group.   
     
     
       2. The silatrane derivative according to claim 1, wherein R 1  is a hydrogen atom or a methyl group, R 4  is a methylene group, and R 5  is a C3 to C10 alkenyl group. 
     
     
       3. A method of preparing a silatrane derivative, said method comprising the step of reacting (i) an epoxy compound having the formula: ##STR12## and (ii) an alkoxysilane compound having the formula:   R.sup.3 Si(OR.sup.6).sub.3     with (iii) a compound selected from the group consisting of ammonia and an amine compound having the formula:     NH.sub.y (CR.sup.1.sub.2 CR.sup.1.sub.2 OH).sub.(3-y)     wherein each R 1  is independently a hydrogen atom or an alkyl group; each R 3  is independently selected from the group consisting of a monovalent hydrocarbon group, a C 1  to C 10  alkoxy group, a glycidoxyalkyl group, an oxiranylalkyl group, an acyloxyalkyl group, a haloalkyl group, and an aminoalkyl group; R 4  is an alkylene group; R 5  is an alkenyl group; R 6  is a C 1  to C 10  alkyl group; and y is 1 or 2.   
     
     
       4. The method according to claim 3, wherein compound (iii) is ammonia and the epoxy compound is used in an amount from 3 to 15 moles per mole of the ammonia. 
     
     
       5. The method according to claim 3, wherein compound (iii) is an amine, y is 1, and the epoxy compound is used in an amount from 0.8 to 5 moles per mole of the amine compound. 
     
     
       6. The method according to claim 3, wherein compound (iii) is an amine, y is 2, and the epoxy compound is used in an amount from 1.8 to 10 moles per mole of the amine compound. 
     
     
       7. The method according to claim 3, wherein the alkoxysilane compound is used in at least about a stoichiometric amount relative to compound (iii). 
     
     
       8. The method according to claim 7, wherein compound (iii) is ammonia and the alkoxysilane compound is used in an amount from 1 to 20 moles per mole of the ammonia. 
     
     
       9. The method according to claim 7, wherein compound (iii) is an amine and the alkoxysilane compound is used in an amount from 1 to 20 moles per mole of the amine compound. 
     
     
       10. The method according to claim 7, wherein the alkoxysilane compound is used in a stoichiometric excess with respect to compound (iii), said method further comprising the step of separating the unreacted alkoxysilane compound from the silatrane derivative. 
     
     
       11. The method according to claim 3, wherein the reaction is carried out at a temperature not greater than 100° C. 
     
     
       12. The method according to claim 3, wherein the reaction is carried out in the presence of an alcohol having the same number of carbon atoms as R 6  in compound (ii). 
     
     
       13. An adhesion promoter comprising the silatrane derivative of claim 1. 
     
     
       14. The adhesion promoter according to claim 13, further comprising an alkoxysilane-containing adhesion promoter. 
     
     
       15. A curable silicone composition, comprising the silatrane derivative of claim 1. 
     
     
       16. The composition according to claim 15, wherein the curable silicone composition is curable by a hydrosilylation reaction. 
     
     
       17. The composition according to claim 15, wherein the silatrane derivative is present in an amount from 0.05 to 10 weight percent based on the total weight of the composition.